Theodore Roosevelt visited San Antonio three times in his life. In 1892, still mourning the fateful day in 1884 when both his mother and first wife died, he came to the Alamo City to hunt javelina. Roosevelt returned in 1898 to recruit and train men for the First U.S. Volunteer Cavalry, which came to be known as the Rough Riders. By the time he made his last trip to San Antonio in 1905, he was president of the United States, attending a banquet honoring him and the other Rough Riders who survived 1898’s Battle of San Juan Hill in Cuba.

While his first sojourn to San Antonio is important as a historian’s statistic, Roosevelt’s second and third stopovers helped put him on Mount Rushmore. And part of his immortality lies in the legend of his bar-side dealings at San Antonio’s Menger Hotel.

Roosevelt was born into a wealthy New York family in 1858 (one year before the Menger opened). He attended Harvard and became a healthy outdoorsman and forceful politician, but the Spanish-American War would soon thrust him into the world’s spotlight in a way that his sickly early years would not have foretold.

At the eve of the twentieth century, the colony of Cuba began fighting for independence from Spain. And on February 15, 1898, the U.S.S. Maine exploded in Havana Harbor, causing the American press to blame the Spanish and call for war (experts now believe the ship’s coal supply spontaneously combusted). When Spain declared war on the U.S. on April 24, 1898, Roosevelt asked permission to start a regiment that would go to Cuba to fight the Spanish.

Congress consented and the U.S. Army made efforts to raise a cavalry regiment comprised only of volunteers. It was to be headed by Colonel Leonard Wood, an Army doctor and the White House physician to President Grover Cleveland, who was awarded the Congressional Medal of Honor for his work as a surgeon during the Apache Campaign of 1886. Roosevelt was serving as Assistant Secretary of the Navy at the time, but was made Wood’s lieutenant-colonel.

Fort Sam Houston’s Quartermaster’s Depot in San Antonio was willing to issue the new regiment horses, so Wood and Roosevelt based operations there. Wood arrived in town May 5, 1898, and set up a recruiting station on the patio of the Menger Hotel, right next to the hotel’s bar. Built one hundred yards from the Alamo (which fell just 23 years before its grand opening in 1859), the Menger Hotel is the oldest continually operating hotel west of the Mississippi. A tourist destination today, it has long been the San Antonio way station, accommodating figures such as Robert E. Lee and Ulysses S. Grant. Roosevelt arrived ten days after Wood on May 15 at the age of 39.

Pre-enlisted men and new volunteers from in and around the Menger Bar arrived, and the Rough Riders were born. The 1,250 men who made up history’s most famous volunteer regiment were Ivy Leaguers, cowboys, East Coast gentlemen, Native Americans, and other assorted adventurers.

They camped south of downtown San Antonio on the International Fair Grounds, now Roosevelt Park, along the historic Missions Trail. Under the Texas sun and Roosevelt’s distinct brand of leadership, they transformed from men into Rough Riders.

They started with the same basic equipment of the Regular Cavalry. They had their Fort Sam Houston horses, and Roosevelt used his ties with the War Department to get his men Krag-Jorgensen carbines, the same weapon issued to Regular U.S. Cavalrymen. But the Rough Riders packed extra equipment to amplify their reputation.

They wore brown canvas stable fatigues and carried machetes in lieu of sabers. Thanks to some New York Rough Riders, including William Tiffany of Tiffany & Company, the group was given 1895 Colt automatic machine guns, an alternative to the Gatling gun mounted on a tripod. The regiment even had a Sims-Dudley dynamite gun, an experimental and unreliable artillery piece that used explosion-driven compressed air to launch a four-and-a-half pound charge of gelatinous “dynamite.”

When they weren’t training, Roosevelt and the Rough Riders spent their time back at the Menger Bar. According to University of Texas at Austin history professor H. W. Brands’ biography T.R.: The Last Romantic, Wood reprimanded Roosevelt for buying beer for the men. Apparently Roosevelt had fraternized with the volunteers to a point Wood felt threatened the gap of rank and respect necessary between an officer and his underlings. Roosevelt responded to Wood, “Sir, I consider myself the damnedest ass within ten miles of this camp! Good night, sir!”

The Rough Riders’ training drew to a close, and they left San Antonio for Tampa Bay, Florida, and on to Cuba July 14, 1898. According to legend, the cavalry regiment was only allowed to bring five horses to Cuba, so Roosevelt and his men charged up Kettle Hill and San Juan Heights on foot, winning Cuban independence in Roosevelt’s immortalized “crowded hour.”

When the Spanish-American War was over, Col. Wood rose to be Army Chief of Staff but had an unsuccessful bid for the presidency. Roosevelt, on the other hand, became the quintessential Rough Rider in the public’s mind and rode his reputation to the vice presidency in 1901. President McKinley was assassinated on September 6 of that year, and eight days later Roosevelt became the nation’s twenty-sixth president. Sworn in at age 42, he is the youngest man to ever hold that post. During his presidency he greatly expanded executive power and redefined foreign policy, setting the United States on the path to becoming the global presence it is today. He lived out “the life of strenuous endeavor” that he prescribed to people everywhere, dying in his sleep January 6, 1919, at age sixty.

The world has not forgotten Teddy Roosevelt, and neither have the patrons and bartenders at the Menger Bar. “People say, ‘Show me those bullet holes in the wall,’” says Ernesto Malacara, the hotel’s longtime director of public relations. He is referring to the legend that Roosevelt fired his gun when making a recruitment speech to the bar’s inhabitants. In truth, the holes appear to be nail or drill holes and don’t match the caliber of any bullet available at the time.

This is one of many myths that has been blown out of proportion by hotel employees who don’t want to disappoint eager guests. They have to tell the tourists something, Malacara insists, but he tries to keep his spiel as accurate as possible. He generally tells visitors that Roosevelt thought the bar was simply a good place to be “looking for adventurers.” He also makes it clear that although Roosevelt probably used the bar as a meeting place, the official recruitment station was outside with Col. Wood.

Unfazed history buffs flock to the two tables on display in the Menger Bar where Roosevelt and Wood purportedly had volunteers sign their enlistment papers to join the Rough Riders. A spotlight also draws their eyes to a picture of Roosevelt in his Rough Rider uniform hanging above the liquor bottles. Among the visitors are members of a Theodore Roosevelt fan club who meet every year at the bar on Roosevelt’s birthday, October 27, to throw back a few brews in honor of Teddy.

“As time goes on, he keeps coming up,” Malacara remarks on the unwavering interest in Roosevelt and his stay in San Antonio. He is still the quintessential Rough Rider, someone on which San Antonio and the Menger can hang their hats and history—which comes as no surprise to Malacara. “The American public is looking for a hero,” he says, “and he was quite a man.”

You'll Love Our Emails

The stories you want, delivered to your inbox.

Enter your email address

I agree to the terms and conditions.

If you fill out the first name, last name, or agree to terms fields, you will NOT be added to the newsletter list. Leave them blank to get signed up.